eicosapentaenoic acid

Eicosapentaenoic Acid is an ω-3 fatty acid and an inhibitor of fatty acid synthase (FASN). Eicosapentaenoic Acid promotes DNA demethylation in the reexpression of the tumor suppressor gene CCAAT/ enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates the RAS/ERK/C/EBPβ pathway in U937 leukemia cells through demethylation of the CpG island of H-RAS intron 1. Eicosapentaenoic Acid promotes the relaxation of vascular smooth muscle cells and vasodilation.

Eicosapentaenoic Acid (EPA) sodium, an orally active omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA), demonstrates a unique ability to demethylate DNA, thereby facilitating the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). This compound also activates the RAS/ERK/C/EBPβ pathway by demethylating H-Ras intron 1 CpG island in U937 leukemia cells and promotes the relaxation of vascular smooth muscle cells, leading to vasodilation.

Eicosapentaenoic acid ethyl ester (Ethyl eicosapentaenoate) is an omega-3 fatty acid.

Heneicosapentaenoic Acid (HPA) is a 21:5 ω-3 fatty acid present in trace amounts in the green alga *B. pennata* and in fish oils. Its structure is similar to eicosapentaenoic acid (EPA) but elongated with one carbon at the carboxyl end, placing the first double bond in the δ6 position. HPA is utilized to study the significance of the position of double bonds in ω-3 fatty acids and incorporates into phospholipids and triacylglycerol in vivo as efficiently as EPA and docosahexaenoic acid. It strongly inhibits arachidonic acid synthesis from linoleic acid, is a poor substrate for prostaglandin H synthase (PGHS) (cyclooxygenase) and 5-lipoxygenase, but rapidly inactivates PGHS.

Eicosapentaenoic acid methyl ester, a degradation product from monogalactosyl diacylglycerol, is an apoptosis-inducing anticancer compound.

Heneicosapentaenoic Acid (HPA), a 21:5 ω-3 fatty acid, is found in minute quantities in green algae and fish oils, resembling eicosapentaenoic acid (EPA) but with an added carbon on the carboxyl end, positioning the initial double bond at the Δ6 location. HPA serves as a tool for examining the impact of double bond positions within n-3 fatty acids, as it is incorporated into phospholipids and triacylglycerol in vivo as efficiently as EPA and docosahexaenoic acid (DHA), while significantly inhibiting the synthesis of arachidonic acid from linoleic acid. Moreover, the ethyl ester variant of heneicosapentaenoic acid offers a more lipophilic and stable alternative to the free acid form.

Heneicosapentaenoic Acid (HPA) is a fatty acid found in small amounts in Bryopsis pennata Lamouroux green algae and fish oils, with a structure similar to eicosapentaenoic acid (EPA), but with an additional carbon at the carboxyl end, resulting in the first double bond being in the Δ6 position. HPA is important for researching the impact of double bond positions in n-3 fatty acids, as it integrates into phospholipids and triacylglycerol in vivo as effectively as EPA and docosahexaenoic acid (DHA), while strongly inhibiting the synthesis of arachidonic acid from linoleic acid. Despite being a poor substrate for prostaglandin H (PGH) synthase and 5-lipoxygenase, HPA can rapidly deactivate PGH synthase. HPA methyl ester, in certain formulations, acts as a prodrug to enhance cellular uptake of HPA before being converted into free acid by esterases, and serves as a useful reference standard.

Eicosapentaenoic Acid-d5 is a deuterated compound of Eicosapentaenoic Acid. Eicosapentaenoic Acid has a CAS number of 10417-94-4. Eicosapentaenoic Acid (EPA) is a ω-3 fatty acid abundantly available in marine organisms.

Eicosapentaenoic Acid (Standard) is the standard substance of Eicosapentaenoic Acid, and it is applicable for quantitative analysis, quality control, and related research in biochemical experiments. Eicosapentaenoic Acid is an ω-3 fatty acid and an inhibitor of fatty acid synthase (FASN). Eicosapentaenoic Acid promotes DNA demethylation in the reexpression of the tumor suppressor gene CCAAT/ enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates the RAS/ERK/C/EBPβ pathway in U937 leukemia cells through demethylation of the CpG island of H-RAS intron 1. Eicosapentaenoic Acid promotes the relaxation of vascular smooth muscle cells and vasodilation.

Eicosapentaenoic acid ethyl ester (Standard) is the standard substance of Eicosapentaenoic acid ethyl ester, and it is applicable for quantitative analysis, quality control, and related research in biochemical experiments. Eicosapentaenoic acid ethyl ester (Ethyl eicosapentaenoate) is an omega-3 fatty acid.

Eicosapentaenoic acid methyl ester (Standard) is the standard substance of Eicosapentaenoic acid methyl ester, and it is applicable for quantitative analysis, quality control, and related research in biochemical experiments. Eicosapentaenoic acid methyl ester is a degradation product derived from monogalactosyl diacylglycerol, which is an apoptosis-inducing anticancer compound.

Eicosapentaenoic Acid-D5 (Standard) is a reference standard of Eicosapentaenoic Acid-D5 intended for quantitative analysis, quality control, and related biochemical research applications. Eicosapentaenoic Acid-d5 is a deuterated compound of Eicosapentaenoic Acid. Eicosapentaenoic Acid has a CAS number of 10417-94-4. Eicosapentaenoic Acid (EPA) is a ω-3 fatty acid abundantly available in marine organisms.

Eicosapentaenoyl Chloride (Eicosapentaenoic acid Chloride; EPA Chloride) is a derivative of eicosapentaenoic acid. It has been utilized in the synthesis of fatty acid conjugates to improve the lipophilicity and cellular permeability of bioactive compounds such as (–)-epigallocatechin gallate and salicylic acid.

Icosabutate (NST-4016) is an orally active derivative of eicosapentaenoic acid that inhibits hepatic inflammation and fibrosis in NASH, improves cardiovascular risk profiles in statin-treated patients with residual hypertriglyceridemia, lowers triglycerides, and may be useful in studies of liver fibrosis and atherosclerosis.

Resolvin E1 (RvE1) is an endogenous lipid mediator derived from the omega-3 fatty acid eicosapentaenoic acid (EPA). It exhibits anti-inflammatory properties, activates inflammation resolution, and promotes phagocytic clearance. It prevents 2,4,6-trinitrobenzenesulfonic acid-induced colitis and improves erythrocytosis and severe aplastic anaemia (SAA).

1,3-Dieicosapentaenoyl glycerol is a diacylglycerol compound featuring eicosapentaenoic acid (EPA) at both the sn-1 and sn-3 positions.

Eicosapentaenoyl-L-carnitine chloride is a long-chain acylcarnitine comprised of Eicosapentaenoic Acid and L-Carnitine. In a mouse model of myopia induced by defocus lenses, mice fed with diets rich in n-3/n-6 polyunsaturated fatty acids (PUFAs) showed increased levels of Eicosapentaenoyl-L-carnitine chloride in their eyes.

Prostaglandin F3α (PGF3α) is a bioactive lipid mediator derived from eicosapentaenoic acid (EPA) with anticancer and anti-inflammatory properties. It serves as a substrate for ABCC4 with a Km of 12.1 μM. Additionally, Prostaglandin F3α (PGF3α) is utilized in diabetes research.

17(18)-EpETE is a 17(18)-epoxy-eicosatetraenoic acid and a metabolite of Eicosapentaenoic acid. It can stimulate outward potassium ion currents and has a relaxing effect on human pulmonary artery and airway smooth muscles.

Resolvin E2 (RvE2) is a member of the specialized pro-resolving mediator (SPM) family of bioactive lipids.1It is produced from eicosapentaenoic acidviaan 18-HEPE intermediate, which is formed by aspirin-acetylated COX-2-mediated oxidation of EPA, by 5-lipoxygenase (5-LO) in human polymorphonuclear (PMN) neutrophils.2,3RvE2 (20 ng/animal) inhibits increases in inflammatory exudate neutrophil infiltration in a mouse model of peritonitis induced by zymosan A .3Hepatic RvE2 levels are increased in mice fed normal chow, as well as in a mouse model of high-fat diet-induced non-alcoholic fatty liver disease (NAFLD), by dietary supplementation with EPA.4Plasma levels of RvE2 are increased by dietary supplementation with fish oil containing ω-3 polyunsaturated fatty acids (PUFAs) in patients with peripheral artery disease or chronic kidney disease.1,5,6 1.Chiang, N., and Serhan, C.N.Specialized pro-resolving mediator network: An update on production and actionsEssays Biochem.64(3)443-462(2020) 2.Tjonahen, E., Oh, S.F., Siegelman, J., et al.Resolvin E2: Identification and anti-inflammatory actions: Pivotal role of human 5-lipoxygenase in resolvin E series biosynthesisChemistry & Biology131193-1202(2006) 3.Sungwhan, F.O., Pillai, P.S., Recchiuti, A., et al.Pro-resolving actions and stereoselective biosynthesis of 18S E-series resolvins in human leukocytes and murine inflammationJ. Clin. Invest.121(2)569-581(2011) 4.Echeverría, F., Valenzuela, R., Espinosa, A., et al.Reduction of high-fat diet-induced liver proinflammatory state by eicosapentaenoic acid plus hydroxytyrosol supplementation: Involvement of resolvins RvE1/2 and RvD1/2J. Nutr. Biochem.6335-43(2019) 5.Ramirez, J.L., Gasper, W.J., Khetani, S.A., et al.Fish oil increases specialized pro-resolving lipid mediators in PAD (the OMEGA-PAD II trial)J. Surg. Res.238164-174(2019) 6.Barden, A.E., Shinde, S., Burke, V., et al.The effect of n-3 fatty acids and coenzyme Q10 supplementation on neutrophil leukotrienes, mediators of inflammation resolution and myeloperoxidase in chronic kidney diseaseProstaglandins Other Lipid Mediat.1361-8(2018)

Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid and docosahexaenoic acid.[1] In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state.[2] Resolvin D1 is produced physiologically from the sequential oxygenation of DHA by 15- and 5-lipoxygenase.[1] 17(R)-RvD1 is an aspirin-triggered epimer of RvD1 that reduces human polymorphonuclear leukocyte (PMN) transendothelial migration, the earliest event in acute inflammation, with equipotency to RvD1 (EC50 = ~30 nM).[3] 17(R)-RvD1 exhibits a dose-dependent reduction in leukocyte infiltration in a mouse model of peritonitis with maximal inhibition of ~35% at a 100 ng dose.[3] In contrast to RvD1, the aspirin-triggered form resists rapid inactivation by eicosanoid oxidoreductases. Analytical and biological comparisons of synthetic 17(R)-RvD1 with endogenously derived 17(R)-RvD1 have confirmed its identity as matching the natural product.[4]

17R(18S)-EpETE is an oxylipin and a cytochrome P450 metabolite of eicosapentaenoic acid .1,217R(18S)-EpETE is an activator of large-conductance calcium-activated potassium (BKCa) channels, increasing the potassium current amplitude by 15-fold in isolated rat cerebral artery vascular smooth muscle cells (VSMCs) at +60 mV when used at a concentration of 50 nM.2It has negative chronotropic effects in isolated neonatal rat cardiomyocytes (NRCMs; EC50= ~1-2 nM) and prevents calcium-induced increases in the spontaneous beating of NRCMs.3,4 1.Schwarz, D., Kisselev, P., Ericksen, S.S., et al.Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: Highly steroselective formation of 17(R), 18(S)-epoxyeicosatetraenoic acidBiochem. Pharmacol.67(8)1445-1457(2004) 2.Lauterbach, B., Barbosa-Sicard, E., Wang, M.H., et al.Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activatorsHypertension39(2 Pt. 2)609-613(2002) 3.Falck, J.R., Wallukat, G., Puli, N., et al.17(R),18(S)-Epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: Structure-activity relationships and stable analoguesJ. Med. Chem.54(12)4109-4118(2011) 4.Arnold, C., Markovic, M., Blossey, K., et al.Arachidonic acid-metabolizing cytochrome P450 enzymes are targets of omega-3 fatty acidsJ. Biol. Chem.285(43)32720-32733(2010)

Leukotriene B5 (LTB5) is a metabolite of eicosapentaenoic acid formed via the 5-lipoxygenase (5-LO) pathway, possessing diverse biological activities, including the ability to increase contraction of bullfrog lung strips ex vivo in a concentration-dependent manner.